DE1907157C3 - Verfahren zur Herstellung eines 1 zu 1-Komplexes von Humulon, katalytisch reduziertem Humulon oder entsprechendem Isohumulon oder von mit Metallboranat reduziertem Isohumulon mit Ammoniak und dessen Verwendung beim Brauen von Bier - Google Patents
Verfahren zur Herstellung eines 1 zu 1-Komplexes von Humulon, katalytisch reduziertem Humulon oder entsprechendem Isohumulon oder von mit Metallboranat reduziertem Isohumulon mit Ammoniak und dessen Verwendung beim Brauen von BierInfo
- Publication number
- DE1907157C3 DE1907157C3 DE1907157A DE1907157A DE1907157C3 DE 1907157 C3 DE1907157 C3 DE 1907157C3 DE 1907157 A DE1907157 A DE 1907157A DE 1907157 A DE1907157 A DE 1907157A DE 1907157 C3 DE1907157 C3 DE 1907157C3
- Authority
- DE
- Germany
- Prior art keywords
- isohumulone
- ammonia
- humulone
- complex
- reduced
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 title claims description 83
- 229910021529 ammonia Inorganic materials 0.000 title claims description 42
- 229930193815 Isohumulone Natural products 0.000 title claims description 31
- RMFGNMMNUZWCRZ-UHFFFAOYSA-N Humulone Natural products CC(C)CC(=O)C1=C(O)C(O)(CC=C(C)C)C(O)=C(CC=C(C)C)C1=O RMFGNMMNUZWCRZ-UHFFFAOYSA-N 0.000 title claims description 30
- QARXXMMQVDCYGZ-UHFFFAOYSA-N isohumulone Chemical compound CC(C)CC(=O)C1=C(O)C(O)(C(=O)CC=C(C)C)C(CC=C(C)C)C1=O QARXXMMQVDCYGZ-UHFFFAOYSA-N 0.000 title claims description 30
- VMSLCPKYRPDHLN-NRFANRHFSA-N humulone Chemical compound CC(C)CC(=O)C1=C(O)C(CC=C(C)C)=C(O)[C@@](O)(CC=C(C)C)C1=O VMSLCPKYRPDHLN-NRFANRHFSA-N 0.000 title claims description 24
- 235000013405 beer Nutrition 0.000 title claims description 16
- 229910052751 metal Inorganic materials 0.000 title claims description 5
- 239000002184 metal Substances 0.000 title claims description 5
- 238000000034 method Methods 0.000 title description 23
- 230000008569 process Effects 0.000 title description 9
- 238000004519 manufacturing process Methods 0.000 title description 6
- BTBUEUYNUDRHOZ-UHFFFAOYSA-N Borate Chemical compound [O-]B([O-])[O-] BTBUEUYNUDRHOZ-UHFFFAOYSA-N 0.000 title 1
- 239000002904 solvent Substances 0.000 claims description 16
- 150000001875 compounds Chemical class 0.000 claims description 6
- 238000002360 preparation method Methods 0.000 claims description 5
- 239000003960 organic solvent Substances 0.000 claims description 4
- 239000002244 precipitate Substances 0.000 description 25
- VLKZOEOYAKHREP-UHFFFAOYSA-N hexane Substances CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 22
- 241000218228 Humulus Species 0.000 description 17
- 239000002253 acid Substances 0.000 description 17
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 16
- 239000000284 extract Substances 0.000 description 16
- JIZQRWKUYFNSDM-UHFFFAOYSA-N 3,4-dihydroxy-2-(3-methylbutanoyl)-5-(3-methylbutyl)-4-(4-methylpentanoyl)cyclopent-2-en-1-one Chemical compound CC(C)CCC1C(=O)C(C(=O)CC(C)C)=C(O)C1(O)C(=O)CCC(C)C JIZQRWKUYFNSDM-UHFFFAOYSA-N 0.000 description 12
- 244000025221 Humulus lupulus Species 0.000 description 10
- 235000008694 Humulus lupulus Nutrition 0.000 description 10
- 229910052799 carbon Inorganic materials 0.000 description 9
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 8
- 238000004458 analytical method Methods 0.000 description 8
- 239000001257 hydrogen Substances 0.000 description 8
- 229910052739 hydrogen Inorganic materials 0.000 description 8
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 8
- 229910052757 nitrogen Inorganic materials 0.000 description 8
- OLHLJBVALXTBSQ-UHFFFAOYSA-N Lupulone Natural products CC(C)CC(=O)C1C(=O)C(CC=C(C)C)C(=O)C(CC=C(C)C)(CC=C(C)C)C1=O OLHLJBVALXTBSQ-UHFFFAOYSA-N 0.000 description 7
- LSDULPZJLTZEFD-UHFFFAOYSA-N lupulone Chemical compound CC(C)CC(=O)C1=C(O)C(CC=C(C)C)=C(O)C(CC=C(C)C)(CC=C(C)C)C1=O LSDULPZJLTZEFD-UHFFFAOYSA-N 0.000 description 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 150000007513 acids Chemical class 0.000 description 6
- WPVSVIXDXMNGGN-UHFFFAOYSA-N beta-bitter acid Natural products CC(C)CC(=O)C1=C(O)C(CC=C(C)C)(CC=C(C)C)C(=O)C(CC=C(C)C)=C1O WPVSVIXDXMNGGN-UHFFFAOYSA-N 0.000 description 6
- 238000001556 precipitation Methods 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- 239000007787 solid Substances 0.000 description 6
- 239000000126 substance Substances 0.000 description 6
- 238000000855 fermentation Methods 0.000 description 5
- 230000004151 fermentation Effects 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 description 4
- -1 dihydrohumulon Chemical compound 0.000 description 4
- 238000000921 elemental analysis Methods 0.000 description 4
- 238000006317 isomerization reaction Methods 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- VZMXLSLKOHIKTQ-UHFFFAOYSA-N Humulon Natural products CC(C)CC(=O)C1=C(O)C(O)(CC=C(C)C)C(=O)C(CC=C(C)C)=C1O VZMXLSLKOHIKTQ-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 230000008901 benefit Effects 0.000 description 3
- ZADPBFCGQRWHPN-UHFFFAOYSA-N boronic acid Chemical compound OBO ZADPBFCGQRWHPN-UHFFFAOYSA-N 0.000 description 3
- 238000013124 brewing process Methods 0.000 description 3
- VMSLCPKYRPDHLN-OAQYLSRUSA-N humulone Chemical compound CC(C)CC(=O)C1=C(O)C(CC=C(C)C)=C(O)[C@](O)(CC=C(C)C)C1=O VMSLCPKYRPDHLN-OAQYLSRUSA-N 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 239000003921 oil Substances 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- 235000019640 taste Nutrition 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- 102000001708 Protein Isoforms Human genes 0.000 description 2
- 108010029485 Protein Isoforms Proteins 0.000 description 2
- 230000032683 aging Effects 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 230000008859 change Effects 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- ZSIAUFGUXNUGDI-UHFFFAOYSA-N hexan-1-ol Chemical compound CCCCCCO ZSIAUFGUXNUGDI-UHFFFAOYSA-N 0.000 description 2
- 229940106579 hops extract Drugs 0.000 description 2
- 239000001906 humulus lupulus l. absolute Substances 0.000 description 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
- 239000002245 particle Substances 0.000 description 2
- 230000009467 reduction Effects 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- 239000001993 wax Substances 0.000 description 2
- WTOFWQARBRVYHI-UHFFFAOYSA-N 3,5,6-trihydroxy-2-(3-methylbutanoyl)-4,6-bis(3-methylbutyl)cyclohexa-2,4-dien-1-one Chemical compound CC(C)CCC1=C(O)C(O)(CCC(C)C)C(=O)C(C(=O)CC(C)C)=C1O WTOFWQARBRVYHI-UHFFFAOYSA-N 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- NHTMVDHEPJAVLT-UHFFFAOYSA-N Isooctane Chemical compound CC(C)CC(C)(C)C NHTMVDHEPJAVLT-UHFFFAOYSA-N 0.000 description 1
- XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical group ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 description 1
- AVAYCNNAMOJZHO-UHFFFAOYSA-N [Na+].[Na+].[O-]B[O-] Chemical compound [Na+].[Na+].[O-]B[O-] AVAYCNNAMOJZHO-UHFFFAOYSA-N 0.000 description 1
- 238000005054 agglomeration Methods 0.000 description 1
- 230000002776 aggregation Effects 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 235000019658 bitter taste Nutrition 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 150000001721 carbon Chemical group 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- JVSWJIKNEAIKJW-UHFFFAOYSA-N dimethyl-hexane Natural products CCCCCC(C)C JVSWJIKNEAIKJW-UHFFFAOYSA-N 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 239000000796 flavoring agent Substances 0.000 description 1
- 235000019634 flavors Nutrition 0.000 description 1
- 238000004108 freeze drying Methods 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 239000002035 hexane extract Substances 0.000 description 1
- 239000011346 highly viscous material Substances 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 230000000977 initiatory effect Effects 0.000 description 1
- 125000000468 ketone group Chemical group 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 239000005445 natural material Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 230000035939 shock Effects 0.000 description 1
- NVIFVTYDZMXWGX-UHFFFAOYSA-N sodium metaborate Chemical compound [Na+].[O-]B=O NVIFVTYDZMXWGX-UHFFFAOYSA-N 0.000 description 1
- 238000010186 staining Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- 238000011282 treatment Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12C—BEER; PREPARATION OF BEER BY FERMENTATION; PREPARATION OF MALT FOR MAKING BEER; PREPARATION OF HOPS FOR MAKING BEER
- C12C3/00—Treatment of hops
- C12C3/04—Conserving; Storing; Packing
- C12C3/08—Solvent extracts from hops
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B22—CASTING; POWDER METALLURGY
- B22D—CASTING OF METALS; CASTING OF OTHER SUBSTANCES BY THE SAME PROCESSES OR DEVICES
- B22D29/00—Removing castings from moulds, not restricted to casting processes covered by a single main group; Removing cores; Handling ingots
- B22D29/04—Handling or stripping castings or ingots
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B66—HOISTING; LIFTING; HAULING
- B66C—CRANES; LOAD-ENGAGING ELEMENTS OR DEVICES FOR CRANES, CAPSTANS, WINCHES, OR TACKLES
- B66C17/00—Overhead travelling cranes comprising one or more substantially horizontal girders the ends of which are directly supported by wheels or rollers running on tracks carried by spaced supports
- B66C17/06—Overhead travelling cranes comprising one or more substantially horizontal girders the ends of which are directly supported by wheels or rollers running on tracks carried by spaced supports specially adapted for particular purposes, e.g. in foundries, forges; combined with auxiliary apparatus serving particular purposes
- B66C17/12—Overhead travelling cranes comprising one or more substantially horizontal girders the ends of which are directly supported by wheels or rollers running on tracks carried by spaced supports specially adapted for particular purposes, e.g. in foundries, forges; combined with auxiliary apparatus serving particular purposes for handling workpieces, e.g. ingots, which require to be supported temporarily within, or withdrawn from, a treatment chamber, e.g. tong cranes, soaking-pit cranes, stripper cranes
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/587—Unsaturated compounds containing a keto groups being part of a ring
- C07C49/703—Unsaturated compounds containing a keto groups being part of a ring containing hydroxy groups
- C07C49/743—Unsaturated compounds containing a keto groups being part of a ring containing hydroxy groups having unsaturation outside the rings, e.g. humulones, lupulones
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12C—BEER; PREPARATION OF BEER BY FERMENTATION; PREPARATION OF MALT FOR MAKING BEER; PREPARATION OF HOPS FOR MAKING BEER
- C12C3/00—Treatment of hops
- C12C3/12—Isomerised products from hops
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Food Science & Technology (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- Mechanical Engineering (AREA)
- General Engineering & Computer Science (AREA)
- General Health & Medical Sciences (AREA)
- Genetics & Genomics (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Distillation Of Fermentation Liquor, Processing Of Alcohols, Vinegar And Beer (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US71261768A | 1968-03-13 | 1968-03-13 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE1907157A1 DE1907157A1 (de) | 1969-11-27 |
| DE1907157B2 DE1907157B2 (de) | 1980-01-31 |
| DE1907157C3 true DE1907157C3 (de) | 1980-10-09 |
Family
ID=24862877
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE1907157A Expired DE1907157C3 (de) | 1968-03-13 | 1969-02-13 | Verfahren zur Herstellung eines 1 zu 1-Komplexes von Humulon, katalytisch reduziertem Humulon oder entsprechendem Isohumulon oder von mit Metallboranat reduziertem Isohumulon mit Ammoniak und dessen Verwendung beim Brauen von Bier |
Country Status (4)
| Country | Link |
|---|---|
| US (1) | US3536495A (enrdf_load_stackoverflow) |
| DE (1) | DE1907157C3 (enrdf_load_stackoverflow) |
| FR (1) | FR2003754A1 (enrdf_load_stackoverflow) |
| GB (1) | GB1188484A (enrdf_load_stackoverflow) |
Families Citing this family (22)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1275732B (de) * | 1965-07-09 | 1968-08-22 | Krupp Gmbh | Zangenkran |
| JPS5250782B2 (enrdf_load_stackoverflow) * | 1972-06-16 | 1977-12-27 | ||
| JPS57183733A (en) * | 1981-04-30 | 1982-11-12 | Sumitomo Chem Co Ltd | Purification of cyclopentenolone |
| US4644084A (en) * | 1984-01-25 | 1987-02-17 | Miller Brewing Company | Preparation of tetrahydroisohumulones |
| US4590296A (en) * | 1984-01-25 | 1986-05-20 | Miller Brewing Company | Process for separation of beta-acids from extract containing alpha-acids and beta-acids |
| EP1299521B1 (en) | 2000-06-30 | 2006-03-08 | S.S. Steiner, Inc. | Improvements to the bittering of beer |
| US7736677B2 (en) * | 2001-06-20 | 2010-06-15 | Metaproteomics, Llc | Xanthohumol and tetrahydro-isoalpha acid based protein kinase modulation cancer treatment |
| US8206753B2 (en) * | 2001-06-20 | 2012-06-26 | Metaproteomics, Llc | Anti-inflammatory botanical products for the treatment of metabolic syndrome and diabetes |
| US8142819B2 (en) | 2002-10-21 | 2012-03-27 | Metaproteomics, Llc | Synergistic compositions that treat or inhibit pathological conditions associated with inflammatory response |
| US8168234B2 (en) | 2001-06-20 | 2012-05-01 | Metaproteomics, Llc | Compositions that treat or inhibit pathological conditions associated with inflammatory response |
| US8158160B2 (en) | 2001-11-13 | 2012-04-17 | Eric Hauser Kuhrts | Anti-inflammatory cyclooxygenase inhibitors |
| US7914831B2 (en) * | 2004-02-27 | 2011-03-29 | Metaproteomics, Llc | Synergistic anti-inflammatory pharmaceutical compositions and related methods using curcuminoids or methylxanthines |
| US20050192356A1 (en) * | 2004-02-27 | 2005-09-01 | Babish John G. | Synergistic anti-inflammatory pharmaceutical compositions and methods of use |
| WO2007021694A2 (en) * | 2005-08-09 | 2007-02-22 | Metaproteomics, Llc | Protein kinase modulation by hops and acacia products |
| US20070154576A1 (en) * | 2005-12-09 | 2007-07-05 | Tripp Matthew L | Protein kinase modulation by hops and Acacia products |
| TW200817027A (en) * | 2006-06-20 | 2008-04-16 | Metaproteomics Llc | Isoalpha acid based protein kinase modulation cancer treatment |
| US20080051466A1 (en) * | 2006-06-20 | 2008-02-28 | Metaproteomics, Llc | Isoalpha acid based protein kinase modulation cancer treatment |
| US8815306B2 (en) * | 2007-03-19 | 2014-08-26 | Metaproteomics, Llc | Methods and compositions for promoting bone and joint health |
| US8241674B2 (en) * | 2007-05-11 | 2012-08-14 | Metaproteomics, Llc | Methods and compositions for heavy metal detoxification |
| AU2008335156A1 (en) * | 2007-12-10 | 2009-06-18 | Metaproteomics, Llc | Substituted 1,3-cyclopentadione multi-target protein kinase modulators of cancer, angiogenesis and the inflammatory pathways associated therewith |
| CA2720546A1 (en) * | 2008-04-02 | 2009-10-08 | Metaproteomics, Llc. | Substituted 1,3-cyclopentadione attenuated endothelial inflammation and endothelial-monocyte interactions |
| GB2594052A (en) | 2020-04-07 | 2021-10-20 | Landa Labs 2012 Ltd | Apparatus for coating a surface with particles |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3143425A (en) * | 1960-07-07 | 1964-08-04 | Chemisches Lab Dr A Mueller | Single-step process of producing hop extracts |
-
1968
- 1968-03-13 US US712617A patent/US3536495A/en not_active Expired - Lifetime
-
1969
- 1969-01-29 GB GB5010/69A patent/GB1188484A/en not_active Expired
- 1969-02-13 DE DE1907157A patent/DE1907157C3/de not_active Expired
- 1969-02-28 FR FR6905342A patent/FR2003754A1/fr not_active Withdrawn
Also Published As
| Publication number | Publication date |
|---|---|
| GB1188484A (en) | 1970-04-15 |
| US3536495A (en) | 1970-10-27 |
| DE1907157A1 (de) | 1969-11-27 |
| DE1907157B2 (de) | 1980-01-31 |
| FR2003754A1 (enrdf_load_stackoverflow) | 1969-11-14 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C3 | Grant after two publication steps (3rd publication) | ||
| 8339 | Ceased/non-payment of the annual fee |